Category: benzothiophene

Related Products of 88-15-3In 2019 ,《A facile synthesis of highly fluorescent pyrido[2,3-d]pyrimidines and 1,8-naphthyridines via oxazine transformation and enaminic addition reactions》 appeared in Journal of the Iranian Chemical Society. The author of the article were El-Sayed, Hassan A.; Morsy, Hesham A.. The article conveys some information:

The synthesis and fluorescence properties of highly substituted bicyclic pyridine derivatives I (Ar = 4-ClC6H4; R = H, CH3, C6H5, 2,4-Cl2C6H3) and 2,2′-(1,3-phenylene)bis(5-(4-chlorophenyl)-7-(thien-2-yl)pyrido[2,3-d]pyrimidin-4(3H)-one), II (R1R2 = -(CH2)4-, -C(O)CH2C(CH3)2CH2-; R1 = C(O)CH3, C6H5; R2 = CH3) and III (R3 = H, SH) are described. The compounds 2-substituted-4-oxo-pyrido[2,3-d]pyrimidines I (Ar = 4-ClC6H4; R = H, CH3, C6H5, 2,4-Cl2C6H3) and 2,2′-(1,3-phenylene)bis(5-(4-chlorophenyl)-7-(thien-2-yl)pyrido[2,3-d]pyrimidin-4(3H)-one) resulted from the acylation reaction of α-aminonicotinonitrile IV with aroyl chlorides RC(O)Cl and isophthaloyl dichloride, di-Et malonate, Et morpholine-4-carboxylate, acetic anhydride or formic acid under solvent-free conditions. The [4 + 2] cyclocondensation and cycloaddition reactions of compound IV with formamide and ammonium thiocyanate tolerated the fused pyrimidines, III resp. Finally, the Friedlander-like reaction was applied for the synthesis of 1,8-naphthyridines II via reaction of compound IV with cyclohexanone, dimedone, acetyl acetone and benzyl Me ketone, resp., under AlCl3 catalysis. The fluorescence spectroscopic data of some synthesized compounds measured and significant results were observed The experimental process involved the reaction of 1-Thiophen-2-yl-ethanone(cas: 88-15-3Related Products of 88-15-3)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. Related Products of 88-15-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

The author of 《Iron-catalyzed oxidative functionalization of C(sp3)-H bonds under bromide-synergized mild conditions》 were Yu, Han; Zhao, Qixin; Wei, Zheyu; Wu, Zhikang; Li, Qi; Han, Sheng; Wei, Yongge. And the article was published in Chemical Communications (Cambridge, United Kingdom) in 2019. COA of Formula: C6H6OS The author mentioned the following in the article:

An efficient oxidation and functionalization of C-H bonds with an inorganic-ligand supported iron catalyst and hydrogen peroxide to prepare the corresponding ketones, e.g., 9H-fluoren-9-one was achieved using the bromide ion as a promoter. Preliminary mechanistic investigations indicated that the bromide ion can bind to FeMo6 to form a supramol. species (FeMo6.2Br), which can effectively catalyze the reaction. In the experiment, the researchers used many compounds, for example, 1-Thiophen-2-yl-ethanone(cas: 88-15-3COA of Formula: C6H6OS)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. COA of Formula: C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Lee, Sunkyung; Lee, Hyunsuk; Yi, Kyu Yang; Lee, Byung Ho; Yoo, Sung-eun; Lee, Kyunghee; Cho, Nam Sook published an article in Bioorganic & Medicinal Chemistry Letters. The title of the article was 《4-Substituted (benzo[b]thiophene-2-carbonyl)guanidines as novel Na+/H+ exchanger isoform-1 (NHE-1) inhibitors》.Electric Literature of C10H7FO2S The author mentioned the following in the article:

A series of 4-substituted (benzo[b]thiophene-2-carbonyl)guanidines, e.g., I, was synthesized and evaluated for the NHE-1 inhibitory activity and cardioprotective efficacy both in vitro and in vivo. Several analogs exhibited a strong inhibition on NHE-1, and which was generally well correlated with their cardioprotective efficacy. Especially the 4-nitro and cyano compounds excellently improved the cardiac function and reduced infarct size against ischemia/reperfusion injury. In the part of experimental materials, we found many familiar compounds, such as Methyl 4-fluorobenzo[b]thiophene-2-carboxylate(cas: 220180-55-2Electric Literature of C10H7FO2S)

Methyl 4-fluorobenzo[b]thiophene-2-carboxylate(cas: 220180-55-2) belongs to benzothiophene.Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. Electric Literature of C10H7FO2SIt has been used as a raw material for the synthesis of biologically active structures and is found in pharmaceuticals such as selective estrogen receptor modulators, leukotriene synthesis inhibitors and antifungals, as well as in many natural products.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Gallazzi, Maria C.; Toscano, Francesca; Paganuzzi, Daniela; Bertarelli, Chiara; Farina, Alessandra; Zotti, Gianni published an article in Macromolecular Chemistry and Physics. The title of the article was 《Polythiophenes with unusual electrical and optical properties based on donor acceptor alternance strategy》.Computed Properties of C7H8O2S The author mentioned the following in the article:

The strategy of donor-acceptor alternation was adopted to reduce the energy gap in substituted polythiophenes; energy gaps down to 1.2 eV were obtained, which is a very low value in the class of polythiophenes. Alkoxy groups and dicyanoethenyl groups were used to prepare electron-rich and electron-poor thiophene units. The copolymers were obtained by coupling reaction methods (Suzuki) and by oxidative chem. and electrochem. polymerization of an opportunely designed substituted terthiophene. X-ray studies and spectroscopic data on the copolymers evidenced that the dicyanoethenyl group as substituent was rather steric demanding and susceptible of side reactions also preventing the n-doping of the material. The conductivity behavior was unusual but compatible with localized charge carriers. The experimental part of the paper was very detailed, including the reaction process of 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Computed Properties of C7H8O2S)

2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3) is one of dioxolane. 1,3-Dioxolane derivatives are recognized as important motifs for the construction of numerous pharmacologically active molecules as antiviral, antifungal, anti-HIV, and adrenoreceptor antagonists.Computed Properties of C7H8O2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Reference of 4-Fluorobenzo[b]thiophene-2-carboxylic acidOn March 1, 2010, Planty, Bruno; Pujol, Chantal; Lamothe, Marie; Maraval, Catherine; Horn, Clemens; Le Grand, Bruno; Perez, Michel published an article in Bioorganic & Medicinal Chemistry Letters. The article was 《Exploration of a new series of PAR1 antagonists》. The article mentions the following:

Two series of new PAR1 antagonists have been identified. The first incorporates a cinnamoylpiperidine motif and the second a cinnamoylpyridine pattern. The synthesis, biol. activity and structure-activity relationship of these compounds are presented. In each series, one analog showed potent in vivo antithrombotic activity in a rat AV shunt model, with up to 53% inhibition at 1.25 mpk iv for compound I. The experimental part of the paper was very detailed, including the reaction process of 4-Fluorobenzo[b]thiophene-2-carboxylic acid(cas: 310466-37-6Reference of 4-Fluorobenzo[b]thiophene-2-carboxylic acid)

4-Fluorobenzo[b]thiophene-2-carboxylic acid(cas: 310466-37-6) belongs to benzothiophene.Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. Reference of 4-Fluorobenzo[b]thiophene-2-carboxylic acidIt has been used as a raw material for the synthesis of biologically active structures and is found in pharmaceuticals such as selective estrogen receptor modulators, leukotriene synthesis inhibitors and antifungals, as well as in many natural products.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 2019,Angewandte Chemie, International Edition included an article by Falconnet, Alban; Magre, Marc; Maity, Bholanath; Cavallo, Luigi; Rueping, Magnus. COA of Formula: C6H6OS. The article was titled 《Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis》. The information in the text is summarized as follows:

Asym. catalysis with readily available, cheap, and nontoxic alk. earth metal catalysts represents a sustainable alternative to conventional synthesis methodologies. In this context, the authors describe the development of a 1st Mg(II)-catalyzed enantioselective hydroboration providing the products with excellent yields and enantioselectivities. NMR spectroscopy studies and DFT calculations provide insights into the reaction mechanism and the origin of the enantioselectivity which can be explained by a metal-ligand cooperative catalysis pathway involving a noninnocent ligand. The experimental process involved the reaction of 1-Thiophen-2-yl-ethanone(cas: 88-15-3COA of Formula: C6H6OS)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. COA of Formula: C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 2019,Applied Organometallic Chemistry included an article by Balamurugan, Gunasekaran; Balaji, Sundarraman; Ramesh, Rengan; Bhuvanesh, Nattamai S. P.. Category: benzothiophene. The article was titled 《Synthesis and Structures of Arene Ruthenium (II)-NHC Complexes: Efficient Catalytic α-alkylation of ketones via Hydrogen Auto Transfer Reaction》. The information in the text is summarized as follows:

A panel of six new arene Ru (II)-NHC complexes (NHC = 1,3-diethyl-(5,6-dimethyl)benzimidazolin-2-ylidene, 1,3-dicyclohexylmethyl-(5,6-dimethyl)benzimidazolin-2-ylidene and 1,3-dibenzyl-(5,6-dimethyl)benzimidazolin-2-ylidene) were synthesized from the transmetallation reaction of Ag-NHC with [(η6-arene)RuCl2]2 and characterized. The ruthenium (II)-NHC complexes were developed as effective catalysts for α-alkylation of ketones and synthesis of bioactive quinoline using primary/amino alcs. as coupling partners resp. The reactions were performed with 0.5 mol% catalyst load in 8 h under aerobic condition and the maximum yield was up to 96%. Besides, the different alkyl wingtips on NHC and arene moieties were studied to differentiate the catalytic robustness of the complexes in the transformations. The experimental process involved the reaction of 1-Thiophen-2-yl-ethanone(cas: 88-15-3Category: benzothiophene)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 1967,Acta Chemica Scandinavica (1947-1973) included an article by Gronowitz, Salo; Persson, Birgitta. Safety of 2-(Thiophen-3-yl)-1,3-dioxolane. The article was titled 《A convenient synthesis of thieno[2,3-b]thiophene》. The information in the text is summarized as follows:

Compound I (0.10 mole) in 30 ml. Et2O was treated dropwise with 89 ml. 1.2N BuLi in Et2O under N, the mixture refluxed 20 min., cooled in ice, 0.10 mole dry S added in small portions, the mixture refluxed 1 hr., cooled, 0.10 mole ClCH2CO2Me in 20 ml. Et2O added dropwise, and, after standing overnight, the mixture added to cold 2N HCl. The solution was extracted with Et2O, the extract dried, added dropwise to a solution of 6.9 g. Na in 200 ml. EtOH, the mixture refluxed 5 hrs., Et2O distilled, and the residue added to H2O and acidified to precipitate 94% II, m. 242-4° (AcOH). Crude II (9.2 g.), 5 g. Cu powder, and 100 ml. quinoline was heated carefully to 180° for 2 hrs. and to 225-30° for 24 hrs., the mixture distilled, the distillate acidified, and the insoluble oil distilled to give 78% title compound (III) b10 95°; picrate m. 135.5-6.5° (MeOH and EtOH). After reading the article, we found that the author used 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Safety of 2-(Thiophen-3-yl)-1,3-dioxolane)

2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3) is one of dioxolane. 1,3-Dioxolane derivatives are recognized as important motifs for the construction of numerous pharmacologically active molecules as antiviral, antifungal, anti-HIV, and adrenoreceptor antagonists.Safety of 2-(Thiophen-3-yl)-1,3-dioxolane

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Cai, Guiping; Yu, Wenying; Song, Dongmei; Zhang, Wenda; Guo, Jianpeng; Zhu, Jiawen; Ren, Yuhao; Kong, Lingyi published an article in European Journal of Medicinal Chemistry. The title of the article was 《Discovery of fluorescent coumarin-benzo[b]thiophene 1, 1-dioxide conjugates as mitochondria-targeting antitumor STAT3 inhibitors》.Safety of Methyl 4-fluorobenzo[b]thiophene-2-carboxylate The author mentioned the following in the article:

STAT3 has been extensively studied as a potential antitumor target. Though studies on regulating STAT3 mainly focus on the inhibition of STAT3 phosphorylation at Tyr705 residue, the phosphorylation at Ser727 residue of STAT3 protein is also closely associated with the mitochondrial import of STAT3 protein. N, N-diethyl-7-aminocoumarin is a fluorescent mitochondria-targeting probe. In this study, a series of STAT3 inhibitors were developed by connecting N, N-diethyl-7-aminocoumarin fluorophore with benzo [b]thiophene 1, 1-dioxide moiety. All designed compounds displayed potent anti-proliferative activity against cancer cells. The representative compound 7a(I) was mainly accumulated in mitochondria visualized by its fluorescence. STAT3 phosphorylation was inhibited by I at both Tyr705 and Ser727 residues. I inhibited STAT3 phosphorylation whereas had no influence on the phosphorylation levels of STAT1, JAK2, Src and Erk1/2, indicating good selectivity of I. Moreover, I down-regulated the expression of STAT3 target genes Bcl-2 and Cyclin D1, increased ROS production and remarkably reduced the mitochondrial membrane potential to induce mitochondrial apoptotic pathway. Furthermore, I in vivo suppressed breast cancer 4T1 implanted tumor growth. Taken together, these results highlighted that I might be a promising mitochondria-targeting STAT3 inhibitor for cancer therapy. The experimental part of the paper was very detailed, including the reaction process of Methyl 4-fluorobenzo[b]thiophene-2-carboxylate(cas: 220180-55-2Safety of Methyl 4-fluorobenzo[b]thiophene-2-carboxylate)

Methyl 4-fluorobenzo[b]thiophene-2-carboxylate(cas: 220180-55-2) belongs to benzothiophene.Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. Safety of Methyl 4-fluorobenzo[b]thiophene-2-carboxylateIt has been used as a raw material for the synthesis of biologically active structures and is found in pharmaceuticals such as selective estrogen receptor modulators, leukotriene synthesis inhibitors and antifungals, as well as in many natural products.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem